CH401075A - Verfahren zur Herstellung von heterocyclischen Verbindungen - Google Patents

Verfahren zur Herstellung von heterocyclischen Verbindungen

Info

Publication number: CH401075A
Authority: CH; Switzerland
Prior art keywords: sep; lysergic acid; methyl; ethanol; blue
Prior art date: 1961-02-03

Application number

CH128461A

Other languages

German (de)

English (en)

Inventor

Albert Dr Hofmann

Franz Dr Troxler

Hans Dr Ott

Original Assignee

Sandoz Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1961-02-03

Filing date

1961-02-03

Publication date

1965-10-31

1961-02-03 Application filed by Sandoz Ag filed Critical Sandoz Ag

1961-02-03 Priority to CH128461A priority Critical patent/CH401075A/de

1962-01-09 Priority to GB892/62A priority patent/GB994486A/en

1962-01-29 Priority to DK522362A priority patent/DK107229C/da

1962-01-29 Priority to LU41167D priority patent/LU41167A1/xx

1962-01-29 Priority to SE979/62A priority patent/SE308320B/xx

1962-01-29 Priority to AT623862A priority patent/AT243991B/de

1962-01-29 Priority to FI0185/62A priority patent/FI40466B/fi

1962-01-29 Priority to ES0274130A priority patent/ES274130A1/es

1965-09-30 Priority to SE12691/65A priority patent/SE309044B/xx

1965-10-31 Publication of CH401075A publication Critical patent/CH401075A/de

1967-05-26 Priority to FI671494A priority patent/FI47485C/fi

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 6
150000002391 heterocyclic compounds Chemical class 0.000 title description 2
150000001412 amines Chemical class 0.000 claims description 13
ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
150000001540 azides Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 23
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
FSIZNIXUPRQTLZ-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC=C2C3=C[C@@H](C(O)=O)CN(C)[C@@H]3CC3=CN=C1[C]32 FSIZNIXUPRQTLZ-QMTHXVAHSA-N 0.000 description 16
WGZBEDCLEXJQGW-IAQYHMDHSA-N (6ar,9r)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CN(C)C3=C1 WGZBEDCLEXJQGW-IAQYHMDHSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
239000002904 solvent Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
QDWITZGTYKPATG-IAQYHMDHSA-N (6aR,9R)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carbohydrazide Chemical compound CN1C=C2C[C@H]3N(C[C@H](C(=O)NN)C=C3C=3C=CC=C1C32)C QDWITZGTYKPATG-IAQYHMDHSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000126 substance Substances 0.000 description 5
-1 1-substituted lysergic acid Chemical class 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 4
229960004943 ergotamine Drugs 0.000 description 4
XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
229930013930 alkaloid Natural products 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229940076279 serotonin Drugs 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
VPMQMZSCCZWHEL-RDTXWAMCSA-N (6aR,9R)-4,7-dimethyl-N-propyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C(CC)NC(=O)[C@H]1CN(C)[C@@H]2CC3=CN(C4=CC=CC(C2=C1)=C34)C VPMQMZSCCZWHEL-RDTXWAMCSA-N 0.000 description 2
VEBWTGYUIBTVNR-MLGOLLRUSA-N (6ar,9r)-n-ethyl-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)NCC)C2)=C3C2=CNC3=C1 VEBWTGYUIBTVNR-MLGOLLRUSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
229950002454 lysergide Drugs 0.000 description 2
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
206010007270 Carcinoid syndrome Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
NESVMZOPWPCFAU-UHFFFAOYSA-N Ergoclavinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-UHFFFAOYSA-N 0.000 description 1
UJYGDMFEEDNVBF-UHFFFAOYSA-N Ergocorninine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 0.000 description 1
241000243251 Hydra Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
YDOTUXAWKBPQJW-UHFFFAOYSA-N alpha-Ergocryptinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-UHFFFAOYSA-N 0.000 description 1
YDOTUXAWKBPQJW-NSLWYYNWSA-N alpha-ergocryptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 description 1
229950001817 alpha-ergocryptine Drugs 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
XQUUDUKVJKNJNP-OGGGUQDZSA-N ergocornine Chemical compound C([C@H]1N(C)C2)C([C]34)=CN=C4C=CC=C3C1=C[C@H]2C(=O)N[C@@]1(C(C)C)C(=O)N2[C@@H](C(C)C)C(=O)N3CCC[C@H]3[C@]2(O)O1 XQUUDUKVJKNJNP-OGGGUQDZSA-N 0.000 description 1
NESVMZOPWPCFAU-ZPRCMDFASA-N ergosine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-ZPRCMDFASA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
SZUQJDJBJHBVBO-CTTKVJGISA-N metergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C=3C=CC=C4N(C)C=C(C=34)C2)=C1)C)C1=CC=CC=C1 SZUQJDJBJHBVBO-CTTKVJGISA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
230000006340 racemization Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH128461A 1961-01-30 1961-02-03 Verfahren zur Herstellung von heterocyclischen Verbindungen CH401075A (de)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
CH128461A CH401075A (de)	1961-02-03	1961-02-03	Verfahren zur Herstellung von heterocyclischen Verbindungen
GB892/62A GB994486A (en)	1961-01-30	1962-01-09	Improvements in or relating to lysergic acid amide derivatives
DK522362A DK107229C (da)	1961-02-03	1962-01-29	Fremgangsmåde til fremstilling af ved indolnitrogenet substituerede amider af lysergsyre- og dihydrolysergsyrerækken.
LU41167D LU41167A1 (da)	1961-01-30	1962-01-29
SE979/62A SE308320B (da)	1961-01-30	1962-01-29
AT623862A AT243991B (de)	1961-02-03	1962-01-29	Verfahren zur Herstellung von neuen an Indolstickstoff substituierten Amiden der Lysergsäure und der Dihydrolysergsäure
FI0185/62A FI40466B (da)	1961-01-30	1962-01-29
ES0274130A ES274130A1 (es)	1961-01-30	1962-01-29	Procedimiento de obtenciën de derivados de acido lisãergico y de acido dihidrolisergico
SE12691/65A SE309044B (da)	1961-01-30	1965-09-30
FI671494A FI47485C (fi)	1961-01-30	1967-05-26	Menetelmä lysergiinihapon tai 9,10-dihydrolysergiinihapon terapeuttisi in tarkoituksiin soveltuvien indolityppeen substituoitujen amidien, va lmistamiseksi.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH128461A CH401075A (de)	1961-02-03	1961-02-03	Verfahren zur Herstellung von heterocyclischen Verbindungen

Publications (1)

Publication Number	Publication Date
CH401075A true CH401075A (de)	1965-10-31

Family

ID=4206819

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH128461A CH401075A (de)	1961-01-30	1961-02-03	Verfahren zur Herstellung von heterocyclischen Verbindungen

Country Status (3)

Country	Link
AT (1)	AT243991B (da)
CH (1)	CH401075A (da)
DK (1)	DK107229C (da)

1961
- 1961-02-03 CH CH128461A patent/CH401075A/de unknown
1962
- 1962-01-29 DK DK522362A patent/DK107229C/da active
- 1962-01-29 AT AT623862A patent/AT243991B/de active

Also Published As

Publication number	Publication date
DK107229C (da)	1967-05-08
AT243991B (de)	1965-12-10

Publication	Publication Date	Title
EP0418716B1 (de)	1994-04-06	Neue Thienylcarbonsäureester von Aminoalkoholen, ihre Quaternierungsprodukte sowie die Herstellung und Verwendung dieser Verbindungen
DE3348334C2 (da)	1992-08-06
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